RU2008147542A - Агонисты мускариновых рецепторов, эффективные при лечении боли, болезни альцгеймера и шизофрении - Google Patents
Агонисты мускариновых рецепторов, эффективные при лечении боли, болезни альцгеймера и шизофрении Download PDFInfo
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- RU2008147542A RU2008147542A RU2008147542/04A RU2008147542A RU2008147542A RU 2008147542 A RU2008147542 A RU 2008147542A RU 2008147542/04 A RU2008147542/04 A RU 2008147542/04A RU 2008147542 A RU2008147542 A RU 2008147542A RU 2008147542 A RU2008147542 A RU 2008147542A
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- RU
- Russia
- Prior art keywords
- alkyl
- alkoxy
- cycloalkyl
- piperidyl
- heterocycloalkyl
- Prior art date
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- 208000024827 Alzheimer disease Diseases 0.000 title claims 3
- 201000000980 schizophrenia Diseases 0.000 title claims 3
- UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 title 1
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 79
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 77
- 239000001257 hydrogen Substances 0.000 claims abstract 77
- 150000002431 hydrogen Chemical class 0.000 claims abstract 63
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 62
- 229910052736 halogen Inorganic materials 0.000 claims abstract 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 49
- 150000002367 halogens Chemical class 0.000 claims abstract 48
- -1 -CH2-OR Chemical group 0.000 claims abstract 47
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 37
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 37
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 23
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 20
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 10
- 239000000203 mixture Substances 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims 237
- 125000003545 alkoxy group Chemical group 0.000 claims 114
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 25
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 22
- 125000003282 alkyl amino group Chemical group 0.000 claims 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 17
- 125000002393 azetidinyl group Chemical group 0.000 claims 15
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 15
- 125000002541 furyl group Chemical group 0.000 claims 15
- 125000003386 piperidinyl group Chemical group 0.000 claims 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 15
- 125000000168 pyrrolyl group Chemical group 0.000 claims 15
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000002757 morpholinyl group Chemical group 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 10
- 125000001544 thienyl group Chemical group 0.000 claims 10
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 9
- 125000004104 aryloxy group Chemical group 0.000 claims 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 9
- 238000000034 method Methods 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 8
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- 230000003993 interaction Effects 0.000 claims 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- RWIIUBCMPVZLBA-UHFFFAOYSA-N 1,3,3a,4,5,6,7,7a-octahydrobenzimidazol-2-one Chemical compound C1CCCC2NC(=O)NC21 RWIIUBCMPVZLBA-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 2
- DBWUZUSWJDAQMD-FGZHOGPDSA-N (3ar,7ar)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-FGZHOGPDSA-N 0.000 claims 1
- LCIHDOOZKXOYAA-RTBURBONSA-N (3ar,7ar)-3-[1-(1-butanoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)CCC)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 LCIHDOOZKXOYAA-RTBURBONSA-N 0.000 claims 1
- CLOVXUMUVUNELE-RTBURBONSA-N (3ar,7ar)-3-[1-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)=C1OC CLOVXUMUVUNELE-RTBURBONSA-N 0.000 claims 1
- HFTYBVTZIUWPKC-NHCUHLMSSA-N (3ar,7ar)-3-[1-[1-(cyclopentanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1CCCC1 HFTYBVTZIUWPKC-NHCUHLMSSA-N 0.000 claims 1
- ACVMDJFCEPWEDE-RTBURBONSA-N (3ar,7ar)-3-[1-[1-(cyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@H]32)=O)CCN1C(=O)C1CC1 ACVMDJFCEPWEDE-RTBURBONSA-N 0.000 claims 1
- CNPPMLHQUZNOFF-YKSBVNFPSA-N (3ar,7as)-1-[1-[1-(2-methylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-3h-indol-2-one Chemical compound CC1=CC=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(C[C@H]3CCCC[C@@H]32)=O)CC1 CNPPMLHQUZNOFF-YKSBVNFPSA-N 0.000 claims 1
- DBWUZUSWJDAQMD-YADHBBJMSA-N (3as,7ar)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-YADHBBJMSA-N 0.000 claims 1
- OFMSVAGCJZSCGP-PMACEKPBSA-N (3as,7as)-1-[1-[1-(cyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3-methyl-3a,4,5,6,7,7a-hexahydrobenzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2N(C1=O)C)C(CC1)CCN1C(CC1)CCN1C(=O)C1CC1 OFMSVAGCJZSCGP-PMACEKPBSA-N 0.000 claims 1
- YKYIFBPVNIHHID-HOTGVXAUSA-N (3as,7as)-3-(1-piperidin-4-ylpiperidin-4-yl)-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound N1([C@H]2CCCC[C@@H]2NC1=O)C(CC1)CCN1C1CCNCC1 YKYIFBPVNIHHID-HOTGVXAUSA-N 0.000 claims 1
- DBWUZUSWJDAQMD-VXKWHMMOSA-N (3as,7as)-3-[1-(1-benzoylpiperidin-4-yl)piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1 DBWUZUSWJDAQMD-VXKWHMMOSA-N 0.000 claims 1
- TXOFDYDHTGBFSI-OALUTQOASA-N (3as,7as)-3-[1-[1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1(C)CC1 TXOFDYDHTGBFSI-OALUTQOASA-N 0.000 claims 1
- CLYBZACMYSDIOQ-PMACEKPBSA-N (3as,7as)-3-[1-[1-(1-methylpyrrole-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CN1C=CC=C1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 CLYBZACMYSDIOQ-PMACEKPBSA-N 0.000 claims 1
- YUOPUHPAOHYNNR-FQECFTEESA-N (3as,7as)-3-[1-[1-(2,2-difluorocyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound FC1(F)CC1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 YUOPUHPAOHYNNR-FQECFTEESA-N 0.000 claims 1
- JNVGUNGAJYNXKS-YIGDWTTGSA-N (3as,7as)-3-[1-[1-(2-methylcyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC1CC1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 JNVGUNGAJYNXKS-YIGDWTTGSA-N 0.000 claims 1
- SFKZMNQERBDWTD-OALUTQOASA-N (3as,7as)-3-[1-[1-(2-methylpropanoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CN(C(=O)C(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SFKZMNQERBDWTD-OALUTQOASA-N 0.000 claims 1
- JYCQGNFNEBGBNB-AHWVRZQESA-N (3as,7as)-3-[1-[1-(2-morpholin-4-ylbenzoyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1N1CCOCC1 JYCQGNFNEBGBNB-AHWVRZQESA-N 0.000 claims 1
- CLOVXUMUVUNELE-OALUTQOASA-N (3as,7as)-3-[1-[1-(3-methoxythiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1OC CLOVXUMUVUNELE-OALUTQOASA-N 0.000 claims 1
- YGSAIPMMUUNJAB-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylfuran-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=COC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1C YGSAIPMMUUNJAB-PMACEKPBSA-N 0.000 claims 1
- SHQRUJGLGJBNCK-PMACEKPBSA-N (3as,7as)-3-[1-[1-(3-methylthiophene-2-carbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1=CSC(C(=O)N2CCC(CC2)N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)=C1C SHQRUJGLGJBNCK-PMACEKPBSA-N 0.000 claims 1
- WAVRRRRZOHOAAA-PMACEKPBSA-N (3as,7as)-3-[1-[1-(cyclobutanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CCC1 WAVRRRRZOHOAAA-PMACEKPBSA-N 0.000 claims 1
- RIUYKDFTYOCUAI-VXKWHMMOSA-N (3as,7as)-3-[1-[1-(cyclohexanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CCCCC1 RIUYKDFTYOCUAI-VXKWHMMOSA-N 0.000 claims 1
- HFTYBVTZIUWPKC-SFTDATJTSA-N (3as,7as)-3-[1-[1-(cyclopentanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CCCC1 HFTYBVTZIUWPKC-SFTDATJTSA-N 0.000 claims 1
- ACVMDJFCEPWEDE-OALUTQOASA-N (3as,7as)-3-[1-[1-(cyclopropanecarbonyl)piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1CC1 ACVMDJFCEPWEDE-OALUTQOASA-N 0.000 claims 1
- BOOWXTRQHJWFBG-FDFHNCONSA-N (3as,7as)-3-[1-[1-[(2r)-1-acetylpyrrolidine-2-carbonyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound CC(=O)N1CCC[C@@H]1C(=O)N1CCC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 BOOWXTRQHJWFBG-FDFHNCONSA-N 0.000 claims 1
- KNGBCSZKNUYXJV-ROUUACIJSA-N (3as,7as)-3-[1-[1-[1-(trifluoromethyl)cyclopropanecarbonyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1(C(F)(F)F)CC1 KNGBCSZKNUYXJV-ROUUACIJSA-N 0.000 claims 1
- GNIWETLLWMGHQG-SFTDATJTSA-N (3as,7as)-3-[1-[1-[3-(2-oxopyrrolidin-1-yl)propanoyl]piperidin-4-yl]piperidin-4-yl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazol-2-one Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)CCN1CCCC1=O GNIWETLLWMGHQG-SFTDATJTSA-N 0.000 claims 1
- IWVLXAWCUVLTGS-GOTSBHOMSA-N 2-[4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carbonyl]benzonitrile Chemical compound C1CC(N2CCC(CC2)N2C(N[C@H]3CCCC[C@@H]32)=O)CCN1C(=O)C1=CC=CC=C1C#N IWVLXAWCUVLTGS-GOTSBHOMSA-N 0.000 claims 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- BIUQRDFLGXLVOH-PMACEKPBSA-N 2-methylpropyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 BIUQRDFLGXLVOH-PMACEKPBSA-N 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 201000007201 aphasia Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- SXVOJMDLKZHJBL-ZWKOTPCHSA-N ethyl 4-[4-[(3as,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@H]32)=O)CC1 SXVOJMDLKZHJBL-ZWKOTPCHSA-N 0.000 claims 1
- SXVOJMDLKZHJBL-ROUUACIJSA-N ethyl 4-[4-[(3as,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(N2C(N[C@H]3CCCC[C@@H]32)=O)CC1 SXVOJMDLKZHJBL-ROUUACIJSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- PYJAXKIMFNHYSK-RTBURBONSA-N propan-2-yl 4-[4-[(3ar,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@H]32)=O)CC1 PYJAXKIMFNHYSK-RTBURBONSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-MOPGFXCFSA-N propan-2-yl 4-[4-[(3ar,7as)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(N[C@@H]3CCCC[C@@H]32)=O)CC1 PYJAXKIMFNHYSK-MOPGFXCFSA-N 0.000 claims 1
- PYJAXKIMFNHYSK-RBUKOAKNSA-N propan-2-yl 4-[4-[(3as,7ar)-2-oxo-3a,4,5,6,7,7a-hexahydro-3h-benzimidazol-1-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1N1CCC(N2C(N[C@H]3CCCC[C@H]32)=O)CC1 PYJAXKIMFNHYSK-RBUKOAKNSA-N 0.000 claims 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 4
- 0 CC(C)N(C(*)C1)C(*)C(*)C1N(C(C**(*)[Al]C1)C1N1)C1=O Chemical compound CC(C)N(C(*)C1)C(*)C(*)C1N(C(C**(*)[Al]C1)C1N1)C1=O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81220906P | 2006-06-09 | 2006-06-09 | |
| US60/812,209 | 2006-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008147542A true RU2008147542A (ru) | 2010-07-20 |
Family
ID=38801727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008147542/04A RU2008147542A (ru) | 2006-06-09 | 2007-06-08 | Агонисты мускариновых рецепторов, эффективные при лечении боли, болезни альцгеймера и шизофрении |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7956069B2 (OSRAM) |
| EP (1) | EP2035411A1 (OSRAM) |
| JP (1) | JP2009539831A (OSRAM) |
| KR (1) | KR20090018210A (OSRAM) |
| CN (1) | CN101501025A (OSRAM) |
| AR (1) | AR061305A1 (OSRAM) |
| AU (1) | AU2007256012A1 (OSRAM) |
| BR (1) | BRPI0712331A2 (OSRAM) |
| CA (1) | CA2654138A1 (OSRAM) |
| EC (1) | ECSP088966A (OSRAM) |
| IL (1) | IL195431A0 (OSRAM) |
| MX (1) | MX2008015136A (OSRAM) |
| NO (1) | NO20085270L (OSRAM) |
| RU (1) | RU2008147542A (OSRAM) |
| SA (1) | SA07280303B1 (OSRAM) |
| TW (1) | TW200813018A (OSRAM) |
| UY (1) | UY30397A1 (OSRAM) |
| WO (1) | WO2007142583A1 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200815405A (en) * | 2006-06-09 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| UY31672A1 (es) * | 2008-02-28 | 2009-09-30 | "agonistas de receptores muscarínicos composiciones farmacéuticas métodos de tratamiento de los mismos, y procedimientos para su preparación" | |
| US20090221642A1 (en) * | 2008-03-03 | 2009-09-03 | Astrazeneca Ab | Muscarinic receptor agonists, compositions, methods of treatment thereof, and processes for preparation thereof-176 |
| US20090275574A1 (en) * | 2008-05-05 | 2009-11-05 | Astrazeneca Ab | Novel compounds-300 |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| CA2753205A1 (en) * | 2009-02-19 | 2010-08-26 | Vanderbilt University | Amidobipiperidinecarboxylate m1 allosteric agonists, analogs and derivatives thereof, and methods of making and using same |
| US20100286124A1 (en) * | 2009-04-10 | 2010-11-11 | Auspex Pharmaceuticals, Inc. | Prop-2-yn-1-amine inhibitors of monoamine oxidase type b |
| CN103068798A (zh) * | 2010-09-03 | 2013-04-24 | 詹森药业有限公司 | 作为单酰甘油脂肪酶抑制剂的二-氮杂环丁烷二酰胺 |
| CN105189482A (zh) | 2013-02-07 | 2015-12-23 | 武田药品工业株式会社 | 作为毒蕈碱m4受体激动剂的哌啶-1-基羧酸酯和氮杂卓-1-基羧酸酯 |
| AU2019247496A1 (en) * | 2018-04-06 | 2020-10-22 | Taro Pharmaceuticals Inc. | Indene derivatives useful in treating pain and inflammation |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3066434D1 (en) | 1979-11-21 | 1984-03-08 | Kyowa Hakko Kogyo Kk | Novel piperidine derivatives, method for the preparation thereof and pharmaceutical compositions containing them |
| DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| ATE216580T1 (de) | 1993-07-16 | 2002-05-15 | Merck & Co Inc | Benzoxazinon- und benzopyrimidinon- piperidinyl- verbindungen als tokolytische oxytocin-rezeptor- antagonisten |
| EP0786997A4 (en) * | 1994-10-27 | 1998-03-11 | Merck & Co Inc | MUSCARINE ANTAGONISTS |
| AU7528696A (en) * | 1995-10-31 | 1997-05-22 | Merck & Co., Inc. | Muscarine antagonists |
| US5756508A (en) * | 1995-10-31 | 1998-05-26 | Merck & Co., Inc. | Muscarine antagonists |
| US5756497A (en) | 1996-03-01 | 1998-05-26 | Merck & Co., Inc. | Tocolytic oxytocin receptor antagonists |
| AU721035C (en) | 1996-09-10 | 2004-09-02 | Dr. Karl Thomae Gmbh | Modified aminoacids, pharmaceuticals containing these compounds and method for their production |
| JPH10158192A (ja) | 1996-10-03 | 1998-06-16 | Eisai Co Ltd | 移植片対宿主疾患（ｇｖｈｄ）の治療および臓器移植時の移植片拒絶反応抑制のための医薬組成物 |
| SE9704546D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| WO1999032481A1 (en) | 1997-12-23 | 1999-07-01 | Alcon Laboratories, Inc. | Muscarinic agents and use thereof to treat glaucoma, myopia and various other conditions |
| JP2000323278A (ja) | 1999-05-14 | 2000-11-24 | Toray Ind Inc | 発光素子 |
| ES2223588T3 (es) | 1999-10-13 | 2005-03-01 | Banyu Pharmaceutical Co., Ltd. | Derivados de imidazolidinona sustituidos. |
| SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
| RU2317988C2 (ru) | 2000-08-14 | 2008-02-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы, фармацевтическая композиция на их основе, применение фармацевтической композиции и способ ингибирования активности катепсина s |
| JP2002302675A (ja) | 2001-04-06 | 2002-10-18 | Fuji Photo Film Co Ltd | 液晶組成物、それを用いた液晶素子およびアゾ化合物 |
| BR0209129A (pt) | 2001-04-18 | 2005-12-20 | Euro Celtique Sa | Compostos, composições farmacêuticas, métodos para tratamento de dores, métodos para modulação de uma resposta farmacológica e usos de compostos |
| PT1975164E (pt) | 2001-04-18 | 2010-04-20 | Euro Celtique Sa | Compostos de octa-hidrobenzimidazolona utilizados como analgésicos |
| US7164024B2 (en) * | 2001-04-20 | 2007-01-16 | Banyu Pharmaceutical Co., Ltd. | Benzimidazolone derivatives |
| WO2004089942A2 (en) | 2001-10-02 | 2004-10-21 | Acadia Pharmaceuticals Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| WO2003028650A2 (en) * | 2001-10-02 | 2003-04-10 | Acadia Pharmaceuticals, Inc. | Benzimidazolidinone derivatives as muscarinic agents |
| EP1451173A4 (en) | 2001-11-01 | 2005-10-26 | Icagen Inc | PIPERIDINE |
| DE60319813T2 (de) | 2002-04-18 | 2009-04-23 | Schering Corporation | 1-(4-piperidinyl)benzimidazole als histamin h3 antagonisten |
| CA2488845A1 (en) * | 2002-06-17 | 2003-12-24 | Merck & Co., Inc. | Opthalmic compositions containing selective m1 muscarinic agonists for treating ocular hypertension |
| JPWO2004069828A1 (ja) * | 2003-02-04 | 2006-05-25 | 三菱ウェルファーマ株式会社 | ピペリジン化合物およびその医薬用途 |
| DE602004008762T2 (de) | 2003-04-30 | 2008-06-12 | The Institutes for Pharmaceutical Discovery, LLC, Branford | Substituierte heteroarylverbindungen als inhibitoren von proteintyrosinphosphatasen |
| US20050250794A1 (en) | 2003-12-19 | 2005-11-10 | Andrew Napper | Methods of treating a disorder |
| US20050228023A1 (en) | 2003-12-19 | 2005-10-13 | Sri International | Agonist and antagonist ligands of the nociceptin receptor |
| CA2568524A1 (en) * | 2004-05-28 | 2005-12-15 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| NZ553696A (en) | 2004-09-13 | 2010-02-26 | Ono Pharmaceutical Co | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient |
| AU2005289453A1 (en) | 2004-09-27 | 2006-04-06 | Government of the United States of America, as represented by the Secretary of the Department of Health and Human Services, National Institutes of Health | Modulating MxA expression |
| WO2006038594A1 (ja) | 2004-10-04 | 2006-04-13 | Ono Pharmaceutical Co., Ltd. | Ｎ型カルシウムチャネル阻害薬 |
| WO2006130469A1 (en) | 2005-05-27 | 2006-12-07 | Oregon Health & Science University | Stimulation of neurite outgrowth by small molecules |
| TW200815351A (en) | 2006-05-02 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| TW200815405A (en) | 2006-06-09 | 2008-04-01 | Astrazeneca Ab | Novel compounds |
| US8119661B2 (en) * | 2007-09-11 | 2012-02-21 | Astrazeneca Ab | Piperidine derivatives and their use as muscarinic receptor modulators |
| UY31672A1 (es) | 2008-02-28 | 2009-09-30 | "agonistas de receptores muscarínicos composiciones farmacéuticas métodos de tratamiento de los mismos, y procedimientos para su preparación" | |
| US20090221642A1 (en) | 2008-03-03 | 2009-09-03 | Astrazeneca Ab | Muscarinic receptor agonists, compositions, methods of treatment thereof, and processes for preparation thereof-176 |
| US20090275574A1 (en) | 2008-05-05 | 2009-11-05 | Astrazeneca Ab | Novel compounds-300 |
-
2007
- 2007-05-29 TW TW096119135A patent/TW200813018A/zh unknown
- 2007-06-07 UY UY30397A patent/UY30397A1/es unknown
- 2007-06-08 CN CNA2007800295059A patent/CN101501025A/zh active Pending
- 2007-06-08 AU AU2007256012A patent/AU2007256012A1/en not_active Abandoned
- 2007-06-08 AR ARP070102507A patent/AR061305A1/es not_active Application Discontinuation
- 2007-06-08 RU RU2008147542/04A patent/RU2008147542A/ru not_active Application Discontinuation
- 2007-06-08 BR BRPI0712331-0A patent/BRPI0712331A2/pt not_active IP Right Cessation
- 2007-06-08 EP EP07748217A patent/EP2035411A1/en not_active Withdrawn
- 2007-06-08 US US11/760,011 patent/US7956069B2/en not_active Expired - Fee Related
- 2007-06-08 WO PCT/SE2007/000554 patent/WO2007142583A1/en not_active Ceased
- 2007-06-08 JP JP2009514231A patent/JP2009539831A/ja not_active Ceased
- 2007-06-08 MX MX2008015136A patent/MX2008015136A/es not_active Application Discontinuation
- 2007-06-08 KR KR1020097000417A patent/KR20090018210A/ko not_active Withdrawn
- 2007-06-08 CA CA002654138A patent/CA2654138A1/en not_active Abandoned
- 2007-06-09 SA SA7280303A patent/SA07280303B1/ar unknown
-
2008
- 2008-11-20 IL IL195431A patent/IL195431A0/en unknown
- 2008-12-12 EC EC2008008966A patent/ECSP088966A/es unknown
- 2008-12-16 NO NO20085270A patent/NO20085270L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ECSP088966A (es) | 2009-01-30 |
| AU2007256012A1 (en) | 2007-12-13 |
| TW200813018A (en) | 2008-03-16 |
| WO2007142583A1 (en) | 2007-12-13 |
| NO20085270L (no) | 2009-01-07 |
| JP2009539831A (ja) | 2009-11-19 |
| BRPI0712331A2 (pt) | 2012-04-03 |
| IL195431A0 (en) | 2009-08-03 |
| CA2654138A1 (en) | 2007-12-13 |
| SA07280303B1 (ar) | 2011-02-23 |
| EP2035411A1 (en) | 2009-03-18 |
| AR061305A1 (es) | 2008-08-20 |
| MX2008015136A (es) | 2008-12-10 |
| US20070287695A1 (en) | 2007-12-13 |
| US7956069B2 (en) | 2011-06-07 |
| CN101501025A (zh) | 2009-08-05 |
| KR20090018210A (ko) | 2009-02-19 |
| UY30397A1 (es) | 2008-01-31 |
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Legal Events
| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110901 |